Perspectives for the Industrial Enzymatic Production of Glycosides

Roode, B. Mattheus de; Franssen, M.C.R.; Padt, A. van der; Boom, R.M.

doi:10.1021/bp030038q

Cited by 104 publications

(54 citation statements)

References 110 publications

(79 reference statements)

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“…In spite of their natural function as hydrolases, the glycosidases can be operated as useful transferases in reversed hydrolysis or transglycosylation reactions. As explained later, ability to suppress hydrolysis and compatibility with polar reactants constitute a much desired combination of solvent properties for glycosylation processes which ionic liquids could arguably provide (for reviews on glycoside synthesis, see de Roode et al, 2003;van Rantwijk et al, 1999).…”

Section: Introduction Ionic Liquids As (Co)solvents For Enzymatic Reamentioning

confidence: 99%

Influence of ionic liquid cosolvent on transgalactosylation reactions catalyzed by thermostable β-glycosylhydrolase CelB fromPyrococcus Furiosus

Lang

Kamrat

Nidetzky

2006

Biotechnol. Bioeng.

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The synthesis of glycosides by enzymatic transglycosylation is a kinetically controlled reaction performed in the context of a non-favorable thermodynamic equilibrium. An unreactive organic cosolvent which increases the selectivity of the enzyme for glycosyl transfer to the acceptor nucleophile compared with water (Ksel) could improve maximum product yield. Here we report on the effect of the ionic liquid 1,3-dimethylimidazoliummethylsulfate on hydrolase and transferase activities of the hyperthermostable beta-glycosidase CelB from the archaeon Pyrococcus furiosus. CelB retained full catalytic efficiency for lactose hydrolysis at 80 degrees C in a 50% (by vol.) solution of ionic liquid in sodium citrate buffer, pH 5.5. It was inactive but not irreversibly denatured at 70% ionic liquid. Using lactose (0.15 M) as galactosyl donor, values of Ksel for a representative series of eight acceptor alcohols were determined in kinetic assays at 80 degrees C and found to increase between 1.3-fold (D-xylose) and 3.1-fold (glycerol) in 45% ionic liquid. Enhancement of Ksel was dependent on ionic liquid concentration and higher than expected from the decrease in water activity caused by the cosolvent. Experimental molar ratios of D-glucose and D-galactose produced during enzymatic conversion of lactose (75-150 mM) in the presence of D-xylose (0.5 M) or glycerol (0.5 M) showed excellent agreement with predictions based on Ksel values and confirm a significant, yet moderate effect of 45% ionic liquid on increasing the yield of D-galactoside product, by < or = 10%.

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Section: Introduction Ionic Liquids As (Co)solvents For Enzymatic Reamentioning

confidence: 99%

Influence of ionic liquid cosolvent on transgalactosylation reactions catalyzed by thermostable β-glycosylhydrolase CelB fromPyrococcus Furiosus

Lang

Kamrat

Nidetzky

2006

Biotechnol. Bioeng.

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“…Owing to the importance of alkyl glycosides as surfactants or as controlled-release precursors of flavor and fragrances, a significant amount of work has been performed to scale up these reactions [54] and scientists are still quite active in this area of applied research.…”

Section: Glycosidases-catalyzed Formation Of Glycosidic Bondsmentioning

confidence: 99%

Hydrolysis and Formation of Glycosidic Bonds

Monti

Riva

2012

Enzyme Catalysis in Organic Synthesis

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Carbohydrates play an important role in many biological events, such as cellular communication and physiological responses. In fact, oligosaccharides and various glycoconjugates have been shown to modulate different molecular recognition processes, including viral and bacterial pathogens recognition [1][2][3][4][5], tumor-associated cell adhesion and metastasis events [6-8], immune response [9], fertilization [10], and neuronal development [11]. This significant role, together with advances in the glycomics field and the recent developments of new synthetic methodologies, for example, the glycorandomization of biologically active natural products [12,13], makes glycoconjugates extremely attractive therapeutic targets nowadays [14][15][16][17].However, the presence of multiple functional groups and stereocenters in carbohydrates makes them challenging targets for organic chemists. Time-consuming protecting group manipulations and complex synthetic schemes are often required to suitably discriminate among hydroxyl groups with similar reactivities and/or to obtain the desired glycosidic linkage by using specifically activated donors and acceptors. Both regioselectivity and stereospecificity need to be strictly controlled and, as the number of different monosaccharide units as well as of glycan structures of interest is very large, a general methodology for oligosaccharide synthesis is still far from being reached. Moreover, despite recent progress in the solid-phase synthesis of oligosaccharides [14,16,18], an automated oligosaccharide synthesizer for all purposes is not yet commercially available and not all the common glycosidic linkages are accessible. Even the structural characterization of the saccharidic part of novel glycoconjugates from natural sources is still a demanding task -no automated sequencing techniques are fully developed, unlike the case of nucleic acids and peptides.Finally, the natural complexity of glycoconjugates is amplified by the extreme variety of aglycon structures coupled to the glycan chains, which can range from Enzyme Catalysis in Organic Synthesis, Third Edition. Edited

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“…The selectivity of these enzymes have been utilized for the preparation of the glycosides, thereby eliminating the need for elaborate protective and de-protective strategies (Roode et al 2003). Thus, the results show that a lipophilic molecule like a-tocopherol could be glycosylated under the reaction conditions employed to produce pharmacologically and therapeutically active water soluble a-tocopheryl glycosides.…”

Section: A-tocopheryl Glycosidesmentioning

confidence: 99%

Syntheses of α-tocopheryl glycosides by glucosidases

et al. 2008

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Enzymatic syntheses of water-soluble alpha-tocopheryl glycosides were carried out in di-isopropyl ether using amyloglucosidase from Rhizopus mold or beta-glucosidase isolated from sweet almond. Optimum conditions for the amyloglucosidase were: alpha-tocopherol 0.5 mmol, D-glucose 0.5 mmol, 400 activity unit (AU) amyloglucosidase, 0.2 mM pH 7 phosphate buffer and 72 h; and for the beta-glucosidase: alpha-tocopherol 0.5 mmol, D: -glucose 0.5 mmol, 110 AU beta-glucosidase, 0.1 mM pH 6 phosphate buffer and 72 h. Out of 11 carbohydrates employed, amyloglucosidase reacted only with D-glucose to give 50% of 6-O-(alpha-D-glucopyranosyl)alpha-tocopherol. However, the beta-glucosidase gave 6-O-(beta-D-glucopyranosyl)alpha-tocopherol, 6-O-(alpha-D-galactopyranosyl)alpha-tocopherol, 6-O-(beta-D-galactopyranosyl)alpha-tocopherol, 6-O-(alpha-D-mannopyranosyl)alpha-tocopherol and 6-O-(beta-D-mannopyranosyl)alpha-tocopherol in yields ranging from 10-25%. Water solubility of 6-O-(alpha-D-glucopyranosyl)alpha-tocopherol was 26 g/l at 25 degrees C. alpha-Tocopheryl glycosides showed antioxidant activities with IC(50) values from 0.5 to 1 mM and angiotensin-converting enzyme (ACE) inhibitory activity with IC(50) values from 1.3 to 2.6 mM.

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Perspectives for the Industrial Enzymatic Production of Glycosides

Cited by 104 publications

References 110 publications

Influence of ionic liquid cosolvent on transgalactosylation reactions catalyzed by thermostable β-glycosylhydrolase CelB fromPyrococcus Furiosus

Influence of ionic liquid cosolvent on transgalactosylation reactions catalyzed by thermostable β-glycosylhydrolase CelB fromPyrococcus Furiosus

Hydrolysis and Formation of Glycosidic Bonds

Syntheses of α-tocopheryl glycosides by glucosidases

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